Hydrochloric Acid → [(4-(4-Methyl-phenyl)pyridine-2-carbonyl)-amino]-acetic acid

HRID 1430198노트

반응식

HRID 1430198 반응식
C[O:2][C:3](=[O:21])[CH2:4][NH:5][C:6]([C:8]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:11]=[CH:10][N:9]=1)=[O:7].O.O[Li].O.Cl>C1COCC1>[CH3:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]2[CH:11]=[CH:10][N:9]=[C:8]([C:6]([NH:5][CH2:4][C:3]([OH:21])=[O:2])=[O:7])[CH:13]=2)=[CH:19][CH:18]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 24891097[(4-(4-Methylphenyl)pyridine-2-carbonyl)amino]-acetic acid methyl ester

생성물 1

HCID 24891149[(4-(4-Methyl-phenyl)pyridine-2-carbonyl)-amino]-acetic acid수율 12%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of [(4-(4-methyl-phenyl)pyridine-2-carbonyl)-amino]-acetic acid methyl ester, 24, (0.092 g, 0.32 mmol) in THF (2 mL) at room temperature is added H2O (1 mL) and LiOH.H2O (0.027 g, 0.64 mmol). The reaction is stirred for 16 hours after which time the solution is acidified using 1M HCl. The solvents are removed under reduced pressure and the solid that remains is suspended in a mixture of THF: MeOH and filtered. The filtrate is concentrated under reduced pressure and the resulting solid is triturated with MeOH and collected by filtration to provide 0.012 g (12% yield) of the desired compound as a colorless solid. 1H NMR (250 MHz, MeOD) δ ppm 8.69 (1H, d, J=4.8 Hz), 8.38 (1H, s), 7.86 (1H, d, J=6.2 Hz), 7.72 (2H, d, J=8.1 Hz), 7.38 (1H, d, J=7.9 Hz), 4.21 (1H, s), 2.44 (2H, s). HPLC-MS: m/z 271 [M+H]+.

후처리

  1. customThe solvents are removed under reduced pressure
  2. additionthe solid that remains is suspended in a mixture of THF
  3. filtrationMeOH and filtered
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe resulting solid is triturated with MeOH
  6. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-638d5ebb0aba476bbfd7456dd4301f9f
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940773B2

반응 노트

불러오는 중…